Falling Out of Love (w/ My Company)

Andrew Draper (@andrewdraper) is a designer and hacker. He’s been an entrepreneur in one way or another for most of his life. He co-founded Manpacks 2 years ago, a service to help guys remember to replace their essentials and give them more time to do the things they’d rather do. Cross-posted with MapleButter.com.

There’s a lot written about having passion and how it’s the key to building something great, but nobody talks about what to do if after you successfully raise a seed round, get thousands of customers and get lots of press/social media attention you find yourself unhappy, unfulfilled or no longer interested in the challenges your startup faces. Here’s how I handled it.

When a spark no longer lights a fire

Years ago I played in a few rock bands, put out a few records and did a small amount of touring—we had a “policy” in each of the bands, something like: “When it stops being fun we’ll stop playing”. I was never the guy who invoked it so I never had to consider what the ramifications of invoking it actually meant—until recently.

I’d had “the thoughts” off/on for a number of months but always attributed them to the normal entrepreneurial roller-coaster of seemingly bi-polar emotions. In early December I flew out to San Francisco for a week and was asked how things were going, with my most recent startup, Manpacks, by a number of people I respect. I came to the realization that I was faking it, and generally being dishonest (especially to myself) every time I answered.

We’d enticed thousands of people to subscribe to Manpacks, received awesome press attention, recently raised a seed round, and hired a developer and a marketer. I was incredibly proud of what we’d achieved (and still am) but at the end of the day I wasn’t fulfilled and felt I could be doing something that interested me more. So, we’d gone to war and in the middle of the battle I was thinking of waving the white flag.

After talking to a few people about how I felt, their answers were all basically the same (paraphrased), “If your passion’s not truly there, life’s too short and you won’t be doing your best work.” I thought to myself, “Wait, they were telling me to abandon ship in the middle of a storm?” That’s the exact opposite of the type of person I see myself as. I had some soul searching to do.

The Breakup—It’s not you, it’s me

That night, I tossed and turned, wondering, how might Ken, my co-founder, react? What would the investors think? I’d helped hire and sell a vision to some great people, what would their reaction be? Was I screwing up everything I’d worked so hard to build over the last 2 years? Did this make me a quitter? Would this make me unable to raise money for my next adventure? I’d had many sleepless nights contemplating. When I awoke the next morning I knew deep down it had to happen, that today was going to be the day.

So, what now?

Practice. Like any good pitch I practiced for an hour or so, running various scenarios to how I thought Ken might react and how to best mitigate the reaction. Fearing he might think I was abandoning him, that I was dumping everything onto him, destroying what we’d built, the list goes on. I feared the worst and practiced every possible way I thought the conversation could go…except one.

After some reflection I made the call…and got voicemail. Ack. A few minutes later my phone rang. Gulp, it was him. I stared at the phone and let it ring probably 3-4 times. I picked it up.

The one scenario I didn’t consider while practicing? Ken totally understanding and taking it all quite well. The truth is, like anything tough or difficult, thinking about it is always worse than the reality of doing it.

I don’t want to put words in Ken’s mouth, but he had realized on his own that my heart was no longer in it. He had sensed I wanted something different and to go on “faking it” would’ve harmed the company more than it would’ve helped it. With that, we put together a plan to make it all work out for the best and allow me to be minimally involved going forward.

Everyone’s happy. Awesome, right? I can work on something I’m truly passionate about and we can all have cookies and milk and go to bed with visions of sugarplums…not quite.

OMG, WTF did I just do?

I still had a few days in California so I worked on some ideas I’d been toying with for awhile, hung out with friends and everything was great. Then I went home, started creating MVP’s, testing ideas and trying to hit on a winning combination for an awesome, fast-growth company. And, my lizard brain took over for a bit. It still does from time to time which means waking up at 3 am, thinking my entire world is collapsing and I’m screwed. It means looking at the bills piling up and wondering WTF I’ve done—you know, the glamorous stuff no one wants to admit is real entrepreneurship.

Me? I love it. Even with the ups/downs. I have no doubt I’ll be able to build another company that’ll leave a dent and I won’t be listenting to my lizard brain, the naysayers or anyone not truly all-in. It might well be a bumpy ride but it’s going to be truly awesome.

It’s been said many times, startups are hard. The only thing that is certain is that there are ups, downs, lefts and rights—and you have to be really good at bobbing and weaving sometimes. BUT, make no mistake they’re even harder when it feels like you’re stuck having to do something you’re really not into anymore. Staying out of loyalty is actually doing more harm than good. I’m not advocating jumping ship as soon as times get tough (which they will), just gut checking to make sure you’re passionate enough to make it through those times. My hope with this post is if you have similar feelings you’ll realize there’s something you can do about it, you just have to be willing to see it through and feel that, no matter what the outcome, you and the company will be better for it (and hopefully learn something in the process).

If you are having similar thoughts, and need someone to bounce what you’re thinking off of, hit me up, I’d be happy to listen and offer any help I can. Otherwise, put your head down and get back to hustling/hacking—there’s gold in them there hills.